Patent GB-1034493-A (GB)
Title: Phosphorus-containing dicarboximides and a method and composition for the control of fungi
IPC: C10M137/16
Filed: 1964-12-21
Abstract: Cutting oils and soaps contain as fungicidal agents compounds of formula RR1P(Z)R11 where Z is O or S; R is (C1- 4 alkyl) amino, C1- 12 alkoxy, C1- 12 alkylthio, C1- 12 alkyl, phenyl, substituted phenyl, phenoxy or substituted phenoxy, which substituted phenyl and phenoxy radicals have from 1-3 substituents, each of which is halo or C1- 4 alkyl; R1 is R or amino; and R11 is a cyclic dicarboximido radical selected from succimido, dichloromaleimido, cyclic hydrocarbon orthodicarboximido and substituted cyclic hydrocarbon ortho-dicarboximido having 1 or 2 substituents selected from halo, NO2, C1- 4 alkyl, methoxy, (C1- 4-alkoxy)-carbonyl and acetamido or 1 to 4 halo substituents alone.  Cyclic hydrocarbon ortho-dicarboximide is defined as phthalimido; partially saturated phthalimido; cyclohexane - 1,2-dicarboximido; norbornane - 2, 3 - dicarboximido; 5 - norbornane - 2,3 - dicarboximido; 7 - oxabicyclo - (2,2,1) - heptane - 2, 3 - dicarboximide and 7 - oxabicyclo - (2,2,1)-hept-5-ene-2, 3-dicarboximide.ALSO:The invention comprises compounds of formula RR1P(Z)R11 where Z is O or S; R is (C1- 4-alkyl)amino, C1- 12 alkoxy, C1- 12 alkylthio, C1- 12 alkyl, phenyl, substituted phenyl, phenoxy or substituted phenoxy, which substituted phenyl and phenoxy radicals have from 1-3 substituents, each of which is halo or C1- 4 alkyl; R1 is R or amino; and R11 is a cyclic dicarboximido radical selected from succimido, dichloromaleimido, cyclic hydrocarbon ortho-dicarboximido and substituted cyclic hydrocarbon ortho-dicarboximido having 1 or 2 substituents selected from halo, NO2, C1- 4 alkyl, methoxy, (C1- 4-alkoxy)-carbonyl and acetamido or 1 to 4 halo substituents alone. Cyclic hydrocarbon ortho-dicarboximide is defined as phathalimido; partially saturated phthalimido; cyclohexane-1,2-dicarboximido; norbornane - 2,3 - dicarboximido; 5 - norbornene - 2,3 - dicarboximido; 7 - oxabicyclo-(2,2,1) - heptane -2,3 - dicarboximide and 7-oxabicyclo - (2,2,1) - hept - 5 - ene - 2,3 - dicarboximide. They are made by reacting an N-alkali metal derivative of the cyclic dicarboximide with RR1P(Z)Cl.ALSO:Fungicidal compositions comprise organophosphorus compounds of formula RR1P(Z)R11 where Z is O or S; R is (C1-4 alkyl) amino, C1-12 alkoxy, C1-12 alkylthio, C1-12 alkyl, phenyl, substituted phenyl, phenoxy or substituted phenoxy, which substituted phenyl and phenoxy radicals have from 1-3 substituents, each of which is halo or C1-4 alkyl; R1 is R or amino; and R11 is a cyclic discarboximido radical selected from succimido, dichloromaleimido, cyclic hydrocarbon orthodicarboximido and substituted cyclic hydrocarbon ortho-dicarboximido having 1 or 2 substituents selected from halo, NO2, C1-4 alkyl, methoxy, C1-4 -alkoxy)-carbonyl and acetamide or 1 to 4 halo substituents alone.  Cyclic hydrocarbon orthodicarboximide is defined as phthalimido; partially saturated phthalimido; cyclohexane-1, 2-dicarboximido; norbornane-2, 3-dicarboximido, 5-norbornane-2, 3-dicarboximido; 7-oxabicyclo (2. 2. 1.)-heptane-2, 3-dicarboximide and 7-oxabicyclo-(2. 2. 1.) hept-5-ene-2, 3-dicarboximide.  Dusts and emulsifiable concentrates and emulsions prepared therefrom are specified.